18390-00-6Relevant articles and documents
Environmentally benign strategy for arylation of nitronyl nitroxide using a non-Transition metal nucleophile
Nakamura, Fumiya,Naota, Takeshi,Suzuki, Shuichi
supporting information, p. 1350 - 1354 (2020/03/13)
We have developed a method for the arylation of nitronyl nitroxide without using its transition metal complex as a nucleophile. Various nitronyl nitroxide-substituted I -electronic compounds can be obtained from the parent nitronyl nitroxide and the corresponding aryl iodides using a combination of zero-valent palladium catalysts and a 2-dicyclohexylphosphino-2′,4′,6′-Triisopropylbiphenyl ligand in the presence of sodium tert-butoxide. The utility of the method has been demonstrated by the direct synthesis of open-shell compounds with giant I -electronic systems, such as 10P.
Synthesis and Straightforward Quantification Methods of Imino Nitroxide-Based Hexaradical Architecture on a Cyclotriphosphazene Scaffold
Fidan, Ismail,?nal, Emel,Yerli, Yusuf,Luneau, Dominique,Ahsen, Vefa,Hirel, Catherine
, p. 11447 - 11453 (2016/11/17)
The synthesis of a homogeneous neutral hexaradical architecture consisting of six imino nitroxide radical moieties covalently bonded on a cyclotriphosphazene scaffold was reported. The synthesis of hexaradical imino nitroxide compounds follows the Ullman procedure involving the condensation of 2,3-bis(hydroxylamino)-2,3-dimethylbutane with hexa-(4-formylphenoxy)cyclotriphosphazene (3) followed by oxidation of the condensation product hexa-[4-(1-hydroxy-4,4,5,5-tetramethyl-2-imidazoline-2-yl)phenoxy]cyclotriphosphazene (2) by NaIO4. Characterization of hexaradical was performed by X-ray and SQUID in solid state and by EPR, absorption spectroscopy, and electrochemistry in solution. CV of 1 shows an oxidation peak at 1.184 V (vs SCE) and a reduction peak at -0.883 V, both characteristics of the presence of phenyl imino nitroxide (7) moieties, suggesting that the contribution of the cyclotriphosphazene core is negligible. Attention was particularly focused on developing methods, UV-vis spectroscopy and square-wave voltammetry, to quantify the number of radicals in a way to confirm easily and rapidly the polyradicals' structure.
A class of novel nitronyl nitroxide labeling basic and acidic amino acids: Synthesis, application for preparing ESR optionally labeling peptides, and bioactivity investigations
Zhang, Jianwei,Zhao, Ming,Cui, Guohui,Peng, Shiqi
, p. 4019 - 4028 (2008/12/22)
Aimed at optional ESR label 2-(4′-hydroxyl)phenyl-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl was introduced into the guanido of l-Arg-OH, the ω-amino group of l-Lys-OH with methylcarboxyl as a linker, and into the β-carboxyl of l-Asp-OH and the γ-carboxyl of l-Glu-OH with ethylamino as a linker. It was explored that the synthetic 30 novel ESR labeling amino acid derivatives were stable enough to the reaction conditions of peptide synthesis. Their incorporation led to 12 novel ESR optionally labeling PAK, RGDS, RGDV, and ECG. A series of NO related chemical tests, the in vitro and in vivo assays of these peptides confirmed that this strategy was practical.
